Will Smith gets mentored by Dave Chappelle in new 'Bucket List' episode

'Life is so much more fun when you don't give a f**k'

American actors Will Smith (left) and Dave Chappelle attend the Canelo Alvarez and Gennady Golovkin middleweight world championship boxing match at T-Mobile Arena.

In a new episode from Will Smith's Facebook Watch series, “Will Smith’s Bucket List," the West Philadelphian native attempts his biggest fear yet - stand-up comedy. Though with a little help from veteran Dave Chappelle, Smith accomplishes it in style.

“The crazy thing is I’m more nervous about doing stand-up than I am about bungee-jumping out of a helicopter over the Grand Canyon," Smiths says in the beginning of the episode.

He seeks counseling from “The Master” aka Dave Chappelle, who invited him to open for one of his show's in only a week's time. When Smith mentions he’s never done stand-up before Chappelle smiles, “This is going to be fun.”

The comedian gives some hearty advice to the newbie with his three rules for stand-up which include "Confidence is key," "Pick the right sh*t to talk about," and "Be interesting all the time." He notes of the last tip, "You have to look at it like you're conducting a conversation with no rebuttal."

Alfonso Ribeiro (Carlton, "Fresh Prince of Bel Air") makes an appearance to give Smith some personal guidance, considering, as Smith notes, the two have known each other for over half their lives. Robeiro says, "Tell us the real reason, the deeper reason for you, as to why you are doing this." Other appearances includes Neal Brennan (co-creator of Chapelle Show), Rell Battle (stand up comedian), and Q-Tip (hip-hop artist).

Chapelle introduces Smith to a sold-out crowd at the Peppermint Club in West Hollywood, Ca. As Jada Picket-Smith cheers on her husband from a booth, he cracks jokes at his wife and kids expense.

He notes of the experience, "Every time I confront a fear, I feel more free. It's what Buddha called "sublime detachment." Life is so much more fun when you don't give a f**k."